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Reflecting on My Failure to Build a Billion-Dollar Company

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Re: Reflecting on My Failure to Build a Billion-Dollar Company

#131
post #109

Earlier quoted context omitted.

Startups. To choose a recent one that turned big, Facebook was approaching such numbers: https://i.guim.co.uk/img/static/sys-images/Guardian/Pix/pict...

Not even close. If you start at 1 million users, 20% monthly growth for 9 years means you would have 13,375,565,248,934 users, or a little over 13 trillion.

Yep. $1M ARR -> $9M ARR right after series A would kill 99% of startups :)

In b2b & esp enterprise, a solid co seems:

* Year 0, 1: $0K-$1M (e.g., POC money or OSS project at another employer) ...

* Year X: $1M ARR * Year X+1: $2-4M ARR (ideally 3X+)

* Year X+2: $5-10M ARR (2X+) * ...

* IPO: $200M+ @ 1.5X growth

That's based on recent IPOs. b/c big seeds and series a concentration, maybe diff for current crop?

The post resonates. It took us awhile on "0->X" b/c we do deep tech vs vanilla saas, and had to get it to the point we can start cranking on more pure-product stuff. So for deep tech co's, you either make no true product and flip, or do a lot of work before even getting to the real business journey.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#132

Earlier quoted context omitted.

Based on the revenue and growth rates of Gumroad my guess is Sahil will make more money from it than he would have at Pinterest. It will take longer but it will be on his terms.

How is that even remotely possible, unless he got no equity in pinterest? They are ~10b IPO'ing this year. Even 1 basis point of pinterest is worth more than what Gumroad brought in.

He owns the majority of Gumroad. Let’s say he had 100 basis points of Pinterest, call it 50% dilution, he’d walk away with $50m. That’s probably very generous, probably actually closer to $20m.

Gumroad will be worth that in a few years at this rate, and he could cash million dollar paychecks along the way if he wanted.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#133

Hey, #1 on Hacker News! I don't think that's happened since...I launched Gumroad back in 2011: https://news.ycombinator.com/item?id=2406614 Thanks HN for being a part of my journey!

Cool! Ive bought multiple video lessons from Gumroad before! Nice to hear from you :)

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#136

Earlier quoted context omitted.

Based on the revenue and growth rates of Gumroad my guess is Sahil will make more money from it than he would have at Pinterest. It will take longer but it will be on his terms.

How is that even remotely possible, unless he got no equity in pinterest? They are ~10b IPO'ing this year. Even 1 basis point of pinterest is worth more than what Gumroad brought in.

1 basis point of $10b is $1m. It's pretty easy to see someone paying him well over that to buy GumRoad at some point.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#137

Earlier quoted context omitted.

I hadn't heard of Gumroad before -- it actually looks like a really good product, and one that I would have occasion to recommend to people. To what do you attribute the challenges? Were you building a product there wasn't a market for, what you were delivering wasn't what people wanted? Or, a marketting failure, inability to get enough people to know about it, and to understand how it would fit their needs? Or, what…

I really tried to avoid being prescriptive about the solutions. It's a lot easier to talk about the problems :) > aren't interested in these questions of what-could-have-been at this point Exactly. If we shipped this or that feature... If we raised more, or less.. If I stayed at Pinterest... If I invested in Bitcoin... I'm just not sure I gain a lot from thoughts like that!

Thanks for sharing this. It's really important not to give too much thought to hypotheticals as they're purely that: a hypothetical.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#138

> It doesn’t matter how amazing your product is, or how fast you ship features. The market you’re in will determine most of your growth. For better or worse, Gumroad grew at roughly the same rate almost every month because that’s how quickly the market determined we would grow. This seems like a simplification, and perhaps overly fatalistic. A company's growth rate is a function with many parameters, and at most poin…

so s/determine most/constrain/

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#139
I had not known about gumroad and took a look. Would you ever introduce more of a product browsing store front experience?

I see all these great categories in the search drop-down, but no way to just take a peak into what was available.

Great read and glad you are enjoying your journey.

Re: Reflecting on My Failure to Build a Billion-Dollar Company

#140

Hey, #1 on Hacker News! I don't think that's happened since...I launched Gumroad back in 2011: https://news.ycombinator.com/item?id=2406614 Thanks HN for being a part of my journey!

Any thoughts on the recent drama on the changes on Patreon and their funding round?
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